In my research I analyze the descriptive metadata of digitized image collections of four art museums in three different countries, selected as they are prominent art institutions situated in countries with legacies of colonialism with collections that potentially reflect these histories. They are also at the forefront of the movement to digitize their collections and have invested in the development of online platforms which make the images available to the public. These institutions face the challenge of working with legacy metadata that could present an obstacle to the goal of inclusive accessibility. By taking a closer look at their institutional metadata the opportunity emerges to compare and contrast how these institutions have dealt with the fraught and often contested histories of their collections.